Japanese Patent 88002418 reports the synthesis of 7,7-dihydro-7-hydroxy(perfluoro-3-oxahepten-1) by chlorinating the methyl ester of perfluoro(3-oxa-1-heptenoic acid), reduction of the chlorinated product with NaBH.sub.4 to give the corresponding alcohol, and then reaction of the alcohol with zinc metal to regenerate the vinyl ether, which is the desired product. It is reported that this compound can be free radically copolymerized with at least one other fluorinated monomer, and optionally non-fluorinated monomers to form useful polymers.
U.S. Pat. No. 4,564,717 reports the synthesis of compounds of the formula CF.sub.2 .dbd.CF(CF.sub.2).sub.m (CH.sub.2).sub.n OH wherein m is an integer from 0 to 10 and n is an integer of 1 to 4. Among the methods of preparation described, is the reduction of the compound CF.sub.2 X.sup.1 CFX.sup.2 CF.sub.2 COOR (sic) wherein R is alkyl and X.sup.1 and X.sup.2 are chlorine or bromine, by various reducing agents. The olefin is then produced by dehalogenation of the alcohol with a metal such as zinc.
European Patent Application 135,917 discloses copolymers of vinylidene fluoride with a compound of the formula CF.sub.2 .dbd.CF(CF.sub.2).sub.m (CH.sub.2).sub.n OH wherein m is 0 to 10 and n is 1-4, and optionally another fluorinated termonomer. Polymers containing fluorovinyl ethers are not disclosed.
European Patent Application 199,138 reports preparation and polymerization (with other fluorine containing olefins) of the compound CF.sub.2 .dbd.CFO(CF.sub.2 CFYO).sub.n (CF.sub.2 CF.sub.2 CH.sub.2 O).sub.m CF.sub.2 CF.sub.2 CH.sub.2 X, wherein X is hydrogen or halogen, Y is fluorine or --CF.sub.3, m is an integer of 0 to 5 and n is 0, 1 or 2. No mention is made of other functional groups being present.
It is the object of this invention to provide trifluorovinyl ether monomers that contain various functional groups. The functional groups may be chemically relatively inert, such as alkyl ether, which when used in a minor proportion in a fluorinated polymer, changes the surfaces properties of that polymer. The functional group may also be more chemically active, such as epoxy, which may be utilized as a crosslinking or adhesion promotion site. Finally the functional group may be styryl or acrylic so that the functional group may be readily polymerized. Also provided are the homo- and copolymers of such compounds, and intermediate compounds from which such trifluorovinyl ethers are made.